So you want to try anal sex. That’s great! Anal play can be lots of fun — if you’re ready for it. Unlike other types of sex, which most people can fumble their way through when they don’t have much experience, anal sex takes some research. (And, to be clear, it’s always better to think and talk through any new sexual experience before you try it with a partner).

But you can’t just slide into anal sex (unless you’re using plenty of lube…but more on that later). If you don’t know what you’re doing and you aren’t careful, you could hurt yourself or your partner because the anus is sensitive. “Contrary to what many believe, anal sex does not have to be painful (unless people engaging in it want it to be),” says Dulcinea Pitagora, a sex therapist known as the Kink Doctor. So before you give anal a try, read our tips about how to prep, both physically and mentally.

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Squirting is a popular porn category, but although it’s not as common IRL, squirting can and does happen — including during anal sex.

As you might already know, squirting, also called female ejaculation, is the name for what happens when fluid “squirts” out of the urethra during sex. This occurs when the Skene’s gland — a gland located inside the anterior wall of the vagina — is stimulated, explains sex and dating coach Myisha Battle. This stimulation makes the Skene’s gland fill with fluid, which is then expressed through the urethra.

“Historically, we thought about stimulation of the G spot contributing to more intense orgasms and the potential for female ejaculation,” Battle explains, but “in the sexological world, we would probably lead more towards calling it the S-spot, because the Skene’s gland is something that, when stimulated, fills with fluid.” Whatever you call it — the G-spot, the S-spot, or the Skene’s gland — you’re going to want to stimulate it through “penetration of some kind, either manually, with a penis or with a toy,” Battle explains. Ideally, she adds, with a “toy that’s curved.”

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Have you ever heard of the “45-degree rule” for anal sex? Well, not many people have. It’s certainly not given the attention it deserves. You can read dozens of articles on the best ways to enjoy anal sex and never hear the rule mentioned. Meanwhile, it’s essentially the key to enjoyable anal play for both men and women… well, besides lube. Always use lots and lots of lube during anal.

The 45-degree rule refers to the angle in which you are tilting a butt plug, anal beads, a dildo, or a penis inside the anus. It’s not this straightforward “stick it in your butt and go” kind of thing.

Like with all things in sex: It’s a bit more complex than that. If you want to take your butt play to the next level, unlocking erogenous zones you may not even know you had, start using the 45-degree rule ASAP.

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So what makes a butt plug different than a dildo or vibrator? While there are many toys designed for anal use, a butt plug tends to have a couple distinguishing characteristics.

A plug is designed to go in and stay in for the duration of its use. While, theoretically, you could absolutely maneuver a plug in and out if you wanted to, folks tend to use dildos for the “in-and-out” sensation. That’s because plugs have a tapered shape that begins small at the top, becomes large in the middle, and tapers back down to a slim diameter at the neck of the toy right before the flared base at the bottom. The thin neck allows for the sphincter to close a bit more so that the plug can be retained inside the body and worn comfortably.

Unlike other anal toys, plugs can easily be worn over longer periods of time. Many people enjoy wearing them for the duration of their playtime, and some folks enjoy going out with a butt plug inserted all night. You can also opt to wear a plug for just a few moments.

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Have you ever heard of anal fingering? It’s exactly what it sounds like — putting a finger (or several) into someone’s anus. And if you’re considering anal sex, anal fingering could be a logical first step. Even if you don’t want to move on to using a penis or dildo for anal, fingering can be erotic for anyone involved. Everyone’s anus has lots of nerve endings around the opening and inside that can feel good when they’re played with. But there are some ground rules you need to learn before you give it a try.

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A reader writes in to an advice column with a question about preferring anal sex:

I DON’T know what is wrong with me. I prefer to have anal sex to vaginal sex. My husband has started complaining that the quality of sex we have has gone down because of that. How can I make things better? — Worried.

This is a fairly common scenario, despite people often not realizing it or thinking there’s something wrong with them for preferring anal. The advice columnist responds:

While enjoying anal is evidently your preference and choice I would advise you to also consider your husband’s needs. He likes vaginal sex, you like anal sex — mix up the two. One round you can have anal the next vaginal or vice versa but just make sure you wash your sex organs before you engage in another type of penetration. It may be vaginal sex is never going to be your thing again. But if there are underlying reasons for avoiding it, exploring and addressing those is sensible, regardless of whether you want to ever have vaginal sex again.

You and your partner clearly need to work out together what feels nice for you, and you are certainly not unique in experiencing a sexual disconnection but it is important to find common ground before it’s too late. Talking to your man is also important as you have mentioned they are OK with anal because you like it, but he might prefer vaginal penetration. Being certain your partner is genuinely fine with anal sex is important, just to be sure they are not going along with it — like you do with vaginal sex.

Advising her to suffer through vaginal sex for his behalf isn’t the best solution. I would instead suggest that she communicate with her husband and see why he thinks sex isn’t as good with her preferring anal, and figure out how to address those concerns while sticking with anal.

While it is possible that he likes vaginal more, that’s a relatively uncommon position to hold once you’ve experienced good anal, so it’s possible that there are just things interfering with anal being as good as it could be for him. Often when discussing the difference, men will agree that it does feel better but complain that it might take more time to prepare for it, make it more difficult to have spontaneous sex, and require that they go slower. All these things can be done with more proactive preparation and training and an increase in the frequency of anal sex. It truly is a scenario where more is better.

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Anonymous: Thanks for the answer! Just to make it clear I didn’t mean “lure” as in “trick”, it was more like “convincing in a challenging an exciting way” and making her feel “part of something” (she already know about my other subs and is okay with that, it’s a whole new world for her and she’s the one who came to me proposing to give anything a try). My fault for not having English as a mother tongue!

Fair enough. So long as she’s consenting and open to and eager about the process and everything involved, then that’s great.

I think focusing primarily on anal is a great idea, and only doing vaginal on rare occasions if she is particularly desperate for it, and reducing the frequency of vaginal over time. Ultimately it all comes down to how she does with just anal and whether she really needs vaginal or does just fine with clit stimulation + anal, etc. If she doesn’t actually need vaginal penetration and enjoys frequent anal, there may not be much reason to continue with vaginal at all.

Everyone is different, so there isn’t any universal answer that works best for everyone. Find something that works for the two of you and work from there.

A woman posts on the Circle of Moms forum, asking whether other women enjoy anal sex:

Ever tried it? If so, do you enjoy it?
I am now at the point where it doesn’t hurt and it will feel good, but only while spooning. 
How about you ladies?

She receives a lot of very positive responses from other women who enjoy or prefer it themselves:

I am at the point where it feels good and I enjoy it more than vaginal.

At one time in my life if would have ask about anal I would have said hell no, But now.. I can honestly say it feel good to me now. A few years ago I had sex with a girl friend of mine, while our husbands were gone a deep sea fishing trip. We played around as usual but while she was licking my clit she put a finger in my ass. She was very good at what she did. It didnt hurt exactly just felt diffrent. She didn’t ram her finger in me it was slow and gentle and just enough I could feel the intensity. I had an orgasm while she licked me and fingered my ass. Afterwars I ask her about it. and she said whe would help me do anal if I wanted to. For months after that when I rubbed myself I would put a finger in my ass also. It became apart of my sexual fun. My husband never knew about my thought on anal. Later when her and I were together again she used 2 fingers and eventually after sometime had passed she fucked me with a dildo in my ass. I don’t think I would have liked it if a man tried anal with me at first, so I’m glad I learned to love it the way I did. Now I love getting fucked in my ass. I want say it feels better than my pussy but it feels diffrent and I enjoy it alot..

My husband and I do anal quite a bit when were are intimate I never thought I would do anal or even like as much as I do. I always thought about trying it but never felt confident enough to bring it up in any relationship I had, But when I met my husband he opened mny eyes to a whole new world and he didnt make me feel uncomfortable he made me feel sexy. i did anal for the first time about 4 months after our daughter was born, one night we were in bed fooling around and he asked me if it would be ok if he went in the other way as he put it and I said are you talking about my butt and he said yes so i said ok but go slow I had never done it and he did go slow he went slow and it was amazing I think the neighbors even heard us…lol

First, the partner (your man or a SO wearing a strap on or even using a dildo) musrt proceed SLOWLY. For me, that means taking at least 5 minutes of very gentle very deliberate short in-and-out movement. Second, a state of mind is required, I have to purposely focus on relaxing but more importantly when I feel the first pressure on my anus I immediately start short grunting-like movements as if I’m trying to have a BM when I’m constipated. I know it is gross to some to mix having a BM with sex but lets be frank … bearing down as when trying to pass a stool actually causes the sphincter muscle to relax and that means LOOSENESS. If you don’t bear down, your back door will be tight and that will hurt. The down side for me is I sometimes let out a small fart or two when my husband is about half way inside my anus but he expects it and knows it is natural. He has been doing my ass occasionally for the past 15 years and I now find it extremely enjoyable.

Don’t know that it’s my favorite, but I have to say my most intense orgasms have been from anal. I became a huge fan of it while I was pregnant for some reason. At that moment, it just worked for me and I asked for it a lot!

A few other women express that they don’t enjoy it, or that it isn’t their favorite, but on the whole everyone is positive about it and encouraging each other to do it more and how to enjoy it. It’s very nice to see a group of women all being positive about anal and helping each other out with it. The world could use more of that. Remember, if you have friends who might be interested in anal, open up to them, share how much you prefer it, and start talking about it and encouraging them to try it for themselves. And if they already like anal, encourage them to try anal only for themselves.

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Anonymous: I am training this young BDSM newbie (she’s 19 and submissive) and she never done anal before, but is willing to give it to me. She’s already sending me a lot of buttspread nudes as I request, so she’s very open and obedient to it. She had two boyfriends before and they were the nerd-beta type and she hated that, wants “someone who can control me not the other way around”. So my goal is: I’m planning to turn her into an AO slave, but maybe not right at the beginning, not to shock her too much. I thought about reversing the typical scenario, fucking her only in the ass 3 or 4 times we meet, then giving her a mixed pussy/assfuck as a “reward” at the following encounter. For how long should I do this before saying AO is a requirement to keep seeing me? What are your thoughts and advices? Also I thought about still letting her be licked on her pussy by other sub girl(s) that I eventually bring into our relationship.

If your intent is to demand strict AO from her, you should be pretty open with her about the fact that you are only interested in anal from the beginning. While a gradual introduction is fine, unless you’re exploring together and seeing where things go together without a clear destination in mind, you should be up front with your intentions rather than trying to “lure” or “trick” her and then demanding anal only from her or you leave her.

Even if she’s submissive, she’s still a person and gets to make decisions too.

Here at the Anal Only Lifestyle, we believe that anal sex should always be pleasurable and pain-free (unless you’re specifically trying to achieve pain in a safe and consensual manner), but unfortunately a common complaint with those first exploring anal is that it hurts and even if it’s something they really want, it can be a challenge for people with little experience to get started without being turned off by painful experiences, past or present.

We have more information on working around this specific issue in the Anal Training section of our Guide to Anal Sex & the Anal Only Lifestyle, but this article will focus specifically on butt plugs and just how great they can be for this purpose.

A Matter of Training & Relaxation

Fundamentally, most people need some level of training and muscle control to relax their anal muscles and be able to open up easily for anal penetration. Warming up those muscles before having sex is an excellent way to help them relax during sex, and inserting a butt plug is a quick and easy way to achieve this.

At the most basic, wearing a butt plug for at least half an hour before having anal sex will help you warm up and be much more relaxed, making sex with a partner or a dildo easier to achieve painlessly.

But beyond that, if you’re really committed to having anal sex regularly and want to have the best experience, start wearing your plug regularly even at times when you aren’t about to have sex. Wear it during the day, during the night, and on days off, and the more you do so, the better and easier anal will become.

A Constant Companion

The more you wear a plug, the more it can help not only benefit your anal training but also amplify your arousal and reinforce your interest in anal sex or the anal only lifestyle. By going about your day with a butt plug inserted, it serves as a steady reminder of anal penetration and keeps you aroused and excited about having your ass filled with something else—whether that be a partner or a toy. It can be a motivating factor, and that excitement and arousal will also help you to relax further and make that subsequent penetration easier for you.

Passive Pleasure

Along the same lines as the above, that presence of a butt plug worn throughout the day provides a delightful sort of passive pleasure and enjoyment in addition to the training benefits you get from it. People wear plugs most often because they feel really good, and you’ll no doubt find the same result. Walking around, sitting down, riding a bicycle or driving, and just generally living your life while receiving constant, passive anal stimulation can be a very enjoyable thing.

What Types of Plugs are Best?

There are so many different butt plugs on the market today, thanks to the steadily growing interest in anal stimulation and sex, but not all are well-suited to the same purposes.

If your goal is training for anal intercourse, you really want to target the anal muscles, and while very slim-necked plugs will still provide some benefit through anal stimulation and arousal helping to relax the anal muscles, the best effect is going to be the result of using a plug with a bit of a thicker neck that helps keep your anal muscles open and relaxed for a longer period of time. Just as the other muscles in your body can be tight and more prone to pain in that state, anal muscles need to be stretched out before use so they’re warmed up and relaxed, and that’s where a thick-necked butt plug really comes into use.

If you want to wear a plug for longer periods of time, comfort is a top priority, and so finding one with a thin, ergonomic base that still serves its purpose of retaining its position comfortably, but without digging into your sensitive skin or causing discomfort. There are a lot of good options out there, and our Guide to Anal Toys offers some suggestions to try out.